CA2880699A1 - Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b - Google Patents
Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b Download PDFInfo
- Publication number
- CA2880699A1 CA2880699A1 CA2880699A CA2880699A CA2880699A1 CA 2880699 A1 CA2880699 A1 CA 2880699A1 CA 2880699 A CA2880699 A CA 2880699A CA 2880699 A CA2880699 A CA 2880699A CA 2880699 A1 CA2880699 A1 CA 2880699A1
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- Prior art keywords
- compound
- mmol
- independently selected
- group
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000011282 treatment Methods 0.000 title claims description 18
- 239000003814 drug Substances 0.000 title description 9
- 208000006454 hepatitis Diseases 0.000 title description 3
- 231100000283 hepatitis Toxicity 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000012453 solvate Substances 0.000 claims abstract description 10
- 239000003112 inhibitor Substances 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 416
- 229910052739 hydrogen Inorganic materials 0.000 claims description 181
- 229920006395 saturated elastomer Polymers 0.000 claims description 120
- 239000001257 hydrogen Substances 0.000 claims description 93
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims description 78
- -1 C1-C3alkyl-R5 Chemical group 0.000 claims description 69
- 125000005842 heteroatom Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 125000005843 halogen group Chemical group 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 208000015181 infectious disease Diseases 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 229930192474 thiophene Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 230000010076 replication Effects 0.000 abstract description 4
- 150000004677 hydrates Chemical class 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 271
- 238000000034 method Methods 0.000 description 252
- 239000000203 mixture Substances 0.000 description 236
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 165
- 238000005160 1H NMR spectroscopy Methods 0.000 description 137
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 123
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 106
- 239000000243 solution Substances 0.000 description 103
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 99
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
- 239000011541 reaction mixture Substances 0.000 description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 92
- 239000012071 phase Substances 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
- 239000012044 organic layer Substances 0.000 description 67
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 65
- 239000002904 solvent Substances 0.000 description 64
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 59
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 55
- 150000002431 hydrogen Chemical group 0.000 description 55
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 54
- 239000003480 eluent Substances 0.000 description 53
- 239000010410 layer Substances 0.000 description 53
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 48
- 230000015572 biosynthetic process Effects 0.000 description 48
- 239000012267 brine Substances 0.000 description 48
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 48
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 46
- 150000001412 amines Chemical class 0.000 description 46
- 229940093499 ethyl acetate Drugs 0.000 description 44
- 235000019439 ethyl acetate Nutrition 0.000 description 44
- 239000007787 solid Substances 0.000 description 43
- 241000700721 Hepatitis B virus Species 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 238000010898 silica gel chromatography Methods 0.000 description 38
- 239000007832 Na2SO4 Substances 0.000 description 36
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
- 229910052938 sodium sulfate Inorganic materials 0.000 description 36
- 235000011152 sodium sulphate Nutrition 0.000 description 36
- 238000010626 work up procedure Methods 0.000 description 36
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 35
- 238000002953 preparative HPLC Methods 0.000 description 35
- 239000007821 HATU Substances 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 30
- 235000019341 magnesium sulphate Nutrition 0.000 description 29
- 239000003208 petroleum Substances 0.000 description 29
- 239000003039 volatile agent Substances 0.000 description 29
- 235000017557 sodium bicarbonate Nutrition 0.000 description 27
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
- NYMDPDNETOLVBS-UHFFFAOYSA-N 4-fluoro-3-methylaniline Chemical compound CC1=CC(N)=CC=C1F NYMDPDNETOLVBS-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 21
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 21
- 239000003960 organic solvent Substances 0.000 description 19
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 16
- 235000011089 carbon dioxide Nutrition 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
- AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- 238000004808 supercritical fluid chromatography Methods 0.000 description 15
- 230000005526 G1 to G0 transition Effects 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 239000012298 atmosphere Substances 0.000 description 12
- 238000010828 elution Methods 0.000 description 12
- 239000005711 Benzoic acid Substances 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 10
- NQTBKYKRAOANGR-UHFFFAOYSA-N 3-[(4-fluoro-3-methylphenyl)carbamoyl]benzenesulfonyl chloride Chemical compound C1=C(F)C(C)=CC(NC(=O)C=2C=C(C=CC=2)S(Cl)(=O)=O)=C1 NQTBKYKRAOANGR-UHFFFAOYSA-N 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XWEBTVZIZWEJOO-UHFFFAOYSA-N 3-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 XWEBTVZIZWEJOO-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 235000010233 benzoic acid Nutrition 0.000 description 9
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 9
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- MIPHRQMEIYLZFZ-BYPYZUCNSA-N (3s)-oxolan-3-amine Chemical compound N[C@H]1CCOC1 MIPHRQMEIYLZFZ-BYPYZUCNSA-N 0.000 description 8
- LMRKXSDOAFUINK-UHFFFAOYSA-N 3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 LMRKXSDOAFUINK-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004007 reversed phase HPLC Methods 0.000 description 8
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 7
- 108020004414 DNA Proteins 0.000 description 7
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 7
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 7
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 7
- 125000002619 bicyclic group Chemical group 0.000 description 7
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 235000017550 sodium carbonate Nutrition 0.000 description 7
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 7
- HIZMJYQEHFJWQY-UHFFFAOYSA-N 1-pyridin-4-ylethanamine Chemical compound CC(N)C1=CC=NC=C1 HIZMJYQEHFJWQY-UHFFFAOYSA-N 0.000 description 6
- IFWSBTBYKXRINT-UHFFFAOYSA-N 3-(difluoromethyl)-4-fluoroaniline Chemical compound NC1=CC=C(F)C(C(F)F)=C1 IFWSBTBYKXRINT-UHFFFAOYSA-N 0.000 description 6
- NQVWMPOQWBDSAI-UHFFFAOYSA-N 3-methyloxetan-3-amine Chemical compound CC1(N)COC1 NQVWMPOQWBDSAI-UHFFFAOYSA-N 0.000 description 6
- PGFQDLOMDIBAPY-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C(F)C(C(F)(F)F)=C1 PGFQDLOMDIBAPY-UHFFFAOYSA-N 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 6
- 229940126179 compound 72 Drugs 0.000 description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 5
- 238000004293 19F NMR spectroscopy Methods 0.000 description 5
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- KYDKEDOKJHAVBZ-UHFFFAOYSA-N 3-(propan-2-ylsulfamoyl)benzoic acid Chemical compound CC(C)NS(=O)(=O)C1=CC=CC(C(O)=O)=C1 KYDKEDOKJHAVBZ-UHFFFAOYSA-N 0.000 description 5
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- BHRZNVHARXXAHW-SCSAIBSYSA-N (2r)-butan-2-amine Chemical compound CC[C@@H](C)N BHRZNVHARXXAHW-SCSAIBSYSA-N 0.000 description 4
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- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 4
- ZUBQTNFHDPACBZ-UHFFFAOYSA-N 3-(cyclopentylsulfamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NC2CCCC2)=C1 ZUBQTNFHDPACBZ-UHFFFAOYSA-N 0.000 description 4
- JCLWHQAZVFXOSC-UHFFFAOYSA-N 3-chloro-4,5-difluoroaniline;hydrochloride Chemical compound Cl.NC1=CC(F)=C(F)C(Cl)=C1 JCLWHQAZVFXOSC-UHFFFAOYSA-N 0.000 description 4
- DFNDHTNAOKAPGX-UHFFFAOYSA-N 3-ethyloxetan-3-amine Chemical compound CCC1(N)COC1 DFNDHTNAOKAPGX-UHFFFAOYSA-N 0.000 description 4
- BEFPEKUQJGOBLX-UHFFFAOYSA-N 3-methyloxetan-3-amine;hydrochloride Chemical compound Cl.CC1(N)COC1 BEFPEKUQJGOBLX-UHFFFAOYSA-N 0.000 description 4
- RGHJWZADAWEIFE-UHFFFAOYSA-N 4-amino-2-methylbenzonitrile Chemical compound CC1=CC(N)=CC=C1C#N RGHJWZADAWEIFE-UHFFFAOYSA-N 0.000 description 4
- HGOBOSIOGKNCFL-UHFFFAOYSA-N 4-fluoro-3-(fluoromethyl)aniline Chemical compound NC1=CC=C(F)C(CF)=C1 HGOBOSIOGKNCFL-UHFFFAOYSA-N 0.000 description 4
- BZXPLADBSZWDIH-VWMHFEHESA-N 4-methylbenzenesulfonic acid;(3s)-oxolan-3-amine Chemical compound N[C@H]1CCOC1.CC1=CC=C(S(O)(=O)=O)C=C1 BZXPLADBSZWDIH-VWMHFEHESA-N 0.000 description 4
- LBYAGWFVZZRAJG-UHFFFAOYSA-N 6-chloro-2-fluoro-3-[(3-methyloxetan-3-yl)sulfamoyl]benzoic acid Chemical compound C=1C=C(Cl)C(C(O)=O)=C(F)C=1S(=O)(=O)NC1(C)COC1 LBYAGWFVZZRAJG-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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CA2857344C (en) | 2011-12-21 | 2019-02-12 | Novira Therapeutics, Inc. | Hepatitis b antiviral agents |
SG10201605291WA (en) * | 2012-08-28 | 2016-08-30 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
SG10201803698UA (en) * | 2012-12-27 | 2018-06-28 | Univ Drexel | Novel antiviral agents against hbv infection |
HUE034820T2 (en) | 2013-02-28 | 2018-02-28 | Janssen Sciences Ireland Uc | Sulphamoyl arylamides and their use as medicaments for the treatment of hepatitis B |
US8993771B2 (en) | 2013-03-12 | 2015-03-31 | Novira Therapeutics, Inc. | Hepatitis B antiviral agents |
EA027068B1 (ru) | 2013-04-03 | 2017-06-30 | Янссен Сайенсиз Айрлэнд Юси | Производные n-фенилкарбоксамида и их применение в качестве лекарственных препаратов для лечения гепатита b |
JO3603B1 (ar) * | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
WO2014184365A1 (en) | 2013-05-17 | 2014-11-20 | Janssen R&D Ireland | Sulphamoylthiophenamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
TR201807090T4 (tr) | 2013-07-25 | 2018-06-21 | Janssen Sciences Ireland Uc | Glioksamid sübstitüeli pirrolamid deriveleri ve bunun hepatitin tedavisine yönelik ilaçlar olarak kullanımı. |
WO2015059212A1 (en) | 2013-10-23 | 2015-04-30 | Janssen R&D Ireland | Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
US9169212B2 (en) | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
US9181288B2 (en) | 2014-01-16 | 2015-11-10 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
AU2015214096B2 (en) | 2014-02-05 | 2021-02-11 | Novira Therapeutics, Inc. | Combination therapy for treatment of HBV infections |
CN110483484A (zh) | 2014-02-06 | 2019-11-22 | 爱尔兰詹森科学公司 | 氨磺酰基吡咯酰胺衍生物及其作为药物用于治疗乙型肝炎的用途 |
KR102363174B1 (ko) | 2014-03-13 | 2022-02-15 | 인디애나 유니버시티 리서치 앤드 테크놀로지 코포레이션 | B형 간염 코어 단백질 알로스테릭 조정제 |
US9400280B2 (en) | 2014-03-27 | 2016-07-26 | Novira Therapeutics, Inc. | Piperidine derivatives and methods of treating hepatitis B infections |
RU2710928C2 (ru) * | 2014-07-31 | 2020-01-14 | Инсерм (Институт Насьональ Де Ла Сант Эт Де Ла Решерш Медикаль) | Антагонисты рецептора flt3 |
US9765050B2 (en) * | 2014-12-30 | 2017-09-19 | Novira Therapeutics, Inc. | Pyridyl reverse sulfonamides for HBV treatment |
MA41338B1 (fr) | 2015-01-16 | 2019-07-31 | Hoffmann La Roche | Composés de pyrazine pour le traitement de maladies infectieuses |
MD20170081A2 (ro) | 2015-03-04 | 2018-03-31 | Gilead Sciences, Inc. | Compuşi 4,6-diamino-pirido[3,2-D]pirimidină modulatori ai receptorilor de tip Toll |
JP2018510159A (ja) * | 2015-03-19 | 2018-04-12 | ノヴィラ・セラピューティクス・インコーポレイテッド | アゾカン及びアゾナン誘導体及びb型肝炎感染症の治療法 |
US10442788B2 (en) | 2015-04-01 | 2019-10-15 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
WO2016183266A1 (en) | 2015-05-13 | 2016-11-17 | Enanta Pharmaceuticals, Inc. | Ehpatitis b antiviral agents |
US10875876B2 (en) * | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
WO2017011552A1 (en) | 2015-07-13 | 2017-01-19 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
US10301255B2 (en) | 2015-07-22 | 2019-05-28 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
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